These boots were designed to feel like a sneaker while standing up to Boston winters

By Rachel Raczka

“If you ask 10 strangers on the street about their snow boots, I doubt any would say they were comfortable,” said Johnson. “But comfort is what people associate with sneakers. And I bet nine of [those strangers] are wearing sneakers. We started thinking about not comparing a new product to other boots, but instead comparing it to what people are already wearing.”

While completing their MBAs at MIT, the founders regularly lamented the need to wear winter boots for several months out of the year. After three years of Boston winters (which, I promise, are horrendous), Johnson and Klein dove into the world of D2C footwear in 2018. Their goal: to invent a shoe that fit their practical parameters but performed like a stylish, everyday sneaker that you wouldn’t dread wearing.

Season Three launched in 2020 with an all-weather, retro-inspired boot called the Ansel. While it’s designed to withstand year-round climate and terrain, their debut product also performs as well as any other snow boot. In creating it, Johnson and Klein debated the reasons why city dwellers consider sneakers their wardrobe workhorses and landed on two factors—they’re lightweight, and they don’t overheat when you go inside—and designed their boot accordingly.

The boot—which comes in waterproof Italian nubuck or long-haired suede—resembles a round-toe, heritage hiker, with D-ring hardware and rugged bottoms. The difference is in the details. The Ansel has a bouncy, lightweight outsole—unlike its bulky 100% rubber counterparts—made from composite materials, designed for comfort without sacrificing grip. It’s lined with New Zealand ZQ-certified merino (a clever tip to fellow footwear innovator AllBirds) for its structural integrity and antimicrobial properties. This complements the Goodyear-welted upper that stitches and seals the boot, rendering it waterproof while allowing the wool to keep your foot cool and dry without the suffocating effects of Gortex.

It was also important to Johnson and Klein to create a boot that was unisex. The Ansel is available online in men’s and women’s sizes with separate SKUs—but in reality, like Converse and many other sneaker brands, Season Three sees no aesthetic or stylistic reason to differentiate between gender in their designs.

Klein attributed the brand’s mindset in part to their Gen Z interns, who helped cultivate a more inclusive experience. He added, “Because of them, and the way they view the world, we wanted to lean into what they were conveying to us and where the world is moving.”

Season Three will release a technical sock next, made in North Carolina, that they view as an ideal pairing with their existing boot. Next comes a technical boot “to be worn in the city and taken off-road if you feel like it,” says Klein, and then a house shoe for just the opposite (“for runs to the deli or to get the mail”) toward the end of the year. 

For now, Klein and Johnson are excited to have wheels back in motion after launching on the cusp of the pandemic from one of the country’s hot spots in March. (“We had 10 beautiful days,” joked Klein.) They’re hoping there’s a silver lining in the country’s “reinvigorated relationship with nature,” seeing it as an outlet for exercise, respite, and freedom.

“We’re more optimistic than we were,” said Johnson. “To begin a startup, you need an insane amount of optimism and to be a little naive. But where we are now, through the fall and the start of this year, we’re so grateful to have momentum.”

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